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22.—Attempted Synthesis of Dibenzo[a,g]biphenylene.*

Published online by Cambridge University Press:  14 February 2012

Neil Campbell ,
R. S. Macpherson  and
R. A. N. Morris
Neil Campbell
Affiliation:
Department of Chemistry, University of Edinburgh
R. S. Macpherson
Affiliation:
Department of Chemistry, University of Edinburgh
R. A. N. Morris
Affiliation:
Department of Chemistry, University of Edinburgh
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Abstract

α-Truxillic acid (1, R = CO2H) (Criegee and Höver 1960) underwent the Arndt-Eistert reaction to yield l,3-diphenylcyclobutane-2,4-diacetic acid (1, R = CH2·CO2H), cyclisation of which with hydrogen fluoride gave cis-trans-cis-5,6,6a,6b, 11,12,12a, 12b-octahydro-5,11-dioxodibenzo[a,g]biphenylene (11). Attempts to aromatise the compound by bromination with N-bromosuccinimide followed by treatment with pyridine or potassium acetate were unsuccessful. The ketone was therefore reduced with potassium borohydride to the corresponding diol (11, CO replaced by CHOH) in the hope that dehydration of the product followed by mild dehydrogenation would yield dibenzo[a,g]biphenylene, but the only product isolated was naphthalene.

Type
Research Article
Information
Proceedings of the Royal Society of Edinburgh Section A: Mathematics , Volume 71 , Issue 4 , 1974 , pp. 275 - 277
Copyright
Copyright © Royal Society of Edinburgh 1974

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References

References to Literature

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